


The Placeholder

by TobytheWise



Category: Supernatural
Genre: Anal Fingering, Bottom Dean Winchester, Creampie, Dirty Talk, Established Relationship, Multi, Plot What Plot/Porn Without Plot, Sex Toys, Skype Sex
Language: English
Status: Completed
Published: 2019-01-19
Updated: 2019-01-19
Packaged: 2019-10-12 23:57:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,712
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17477396
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: Every week, Dean, Cas, and Benny have a skype date. This week Dean has something very special in mind now that he’s finally used the Bad Dragon gift card Benny gave him for Christmas.





	The Placeholder

Dean props himself up on one elbow, tilting his laptop screen just right to show off his face and the top of his chest before answering the call. His two favorite faces show up on the split screen, each in a different location. Dean’s heart longs to be in their arms again but for now he’s gotta settle for their weekly skype date. 

“Hello, Dean,” Cas says, waving into the camera. “Hello, Benny.”

Dean smiles as Benny greets them. “Hey there, Hot Wings. Howdy, Sugar.”

“I miss you guys,” Dean murmurs, his cheeks reddening with the confession. He tries to keep these skype dates light and happy but today he just really misses his men. Especially after being with them for so long during Christmas break. 

“Last semester,” Benny says. 

“One more semester for you and Benny and then you’ll both be able to come here. We’ll all get an apartment together while I finish,” Cas adds. 

Dean nods his head. “I know. I’m sorry to bring the call down. I’m just really missing you guys.”

“It’s alright, cher. I miss you too. And I miss you, Cas. Soon enough we’ll be together again. Until then, we’ll just enjoy our weekly skype dates.”

“Tell us what’s new, Dean,” Cas says, getting more comfortable on his bed. 

Dean takes a deep breath. “Well,” he starts, his belly warm with anticipation. “I have my dorm room to myself today.”

“Oh really,” Benny says, his southern accent making Dean melt like it always does. “How did ya manage that?”

“I told my roommate I was having skype sex with my boyfriends and he didn’t wanna be a part of it so he ran pretty quick.”

Cas and Benny both groan, their faces beginning to flush beautifully as their arousal starts to take over. Dean couldn’t help himself from smirking as he slowly tilts his laptop down, showing off more of his bare chest.

“Dean,” Benny and Cas say at the same time, their voices roughening. 

“Show me some skin, Cas,” Dean says, running his right hand up and down his chest. “I have quite the surprise for you both but I wanna see some of you both first.”

Cas stands up, his torso filling the whole screen as those long fingers begin to unbutton his dress shirt. Dean’s always had a thing for Cas only showing off as much as Dean asks for. There’s just something inexplicably sexy about Cas only opening his dress slacks, pulling out his hard dick, and fucking Dean with all his clothes still on. 

Once Cas’ shirt is unbuttoned, he pulls it open, showing off his toned stomach to the camera. “Fuck,” Dean whispers, staring at his boyfriend’s sexy body. There’s an answering growl of approval from Benny. 

And then the giant tease sits back down. His torso deliciously naked with his shirt pulled open, just the way that gets Dean the most hot and bothered. 

“Your turn, Benny,” Cas states, his voice deeper now that they’ve started their little game. 

Benny tosses his hat off, throwing it behind himself and Dean lets out a little giggle. His big ol bear is adorable. Benny takes his time unbuttoning his shirt and Dean can’t help but squirm. His cock is hard against his belly, throbbing with need. Once the shirt is off, leaving Benny’s top completely bare, he smirks into the camera. “Ya like what ya see, boys?”

“Very much so,” Cas answers. 

“You’re both so sexy. I could sit here and look at you both for hours,” Dean murmurs, his hand fisting his bed sheet so he won’t reach for his cock. Not yet. “Would you like to know the game I have planned?”

They both nod their heads, gesturing for him to go on. “Well, I may have finally used that gift card Benny gave me for Christmas. Would you like me to show you?”

“Oh fuck,” Benny gasps out.

“You both get to take turns telling me exactly what you want me to do,” Dean says, his voice sounding calmer than he’s feeling on the inside. 

“Get naked,” Cas says first. “Wanna see you, gorgeous.”

Dean smirks into the camera before stretching out across his bed, aiming his camera to show off his entire body which is completely bare. His cock sits heavy between his legs, begging for attention but for now, Dean can ignore it. He loves being bossed around by his men. 

“Holy shit, mon cher. Look at you. So beautiful,” Benny murmurs. “Play with your nipples. Wanna see them all hard and aching.”

Dean’s hands move over his chest. He starts up at his collarbone, the light touch making his skin prickle with pleasure. Once at his nipples, he starts light, running the pads of his fingers over the nubs until they harden under his touch. 

“Pinch them,” Cas says, authority in his voice. 

“Fuck,” Dean gasps as he does what he’s told. Pleasure zings through his spine as he pinches his nipples, tormenting himself with the flood of pain that makes his cock jerk. He loves this. 

“Can you move your laptop again, Sugar? Wanna see all of you,” Benny says and when Dean finally opens his eyes again, he notices that both of his boyfriends are rubbing their cocks through their pants. 

Dean quickly shuffles things around until his laptop sits on an end table at the end of his bed. Dean sits on his bed, his legs spread, giving his boyfriends the perfect view of all of him including his spread thighs, hole, balls, and straining cock. 

“Shit,” one of them hisses and Dean’s chest flushes with pleasure. 

“What next?” he asks, his voice breathy with want. 

“Touch your sac,” Cas tells him. “Roll them around in your palm. Tug on them just the way you like.”

“Wanna hear your pretty noises, Cher.”

Dean tilts his head up towards the ceiling as one of his hands touches his balls. They’re freshly smooth from his shower earlier, knowing he wanted to be shaved and ready for their date. He rolls them between his fingers, moaning as they draw up tighter, wanting to empty already. A gasp leaves his throat as he tugs them, the pleasure pain balance just right.

“Fuck, Dean,” Benny murmurs, forcing Dean to open his eyes and look back at his laptop. He bites his lip as he watches the looks of matching lust on each of their faces. “Tease your hole for us, Dean.”

Dean’s hand moves lower, rubbing against his dry hole. He tenses the muscle, hearing moans from his men as they watch his ass blink at them. Dean taps his hole a few times, feeling his entire body tense with the urge to push his finger in but he waits. Because he’s a good boy and he wants to play the game. 

“Please,” he whimpers when neither of them say anything. 

Spurred on, Cas asks, “do you have lube?”

“Yes. Please,” Dean whines. “Please let me finger myself. Please. Wanna be filled so badly.”

Benny lets out a little chuckle. “Our perfect little bottom.”

It’s no secret that of the three of them, Dean’s the one that loves to bottom the most. There’s nothing quite like the feeling of being stuffed full and demanded to come from only the feel of a dick in his ass, rubbing against his prostate. Castiel is their dominante partner, thriving off being in control regardless if he’s bottoming or topping. And Benny is their big soft bear knowing when to be sweet and when to be growly. He loves on them and gives them the sappy love making they crave while also being their exclusive top. The three of them just fit so perfectly, needing all of them together to be this happy and content. 

Dean quickly grabs the lube, covering his fingers before shoving his middle finger fully inside his ass. No more teasing, no more waiting, just the sweet bliss that comes with finally being penetrated. “Oh fuck,” he moans as he adds a second finger, loving the slight burn that comes with stretching himself. 

“Fucking hell,” Cas murmurs. When Dean looks at the screen, he lets out another whine. Cas finally has his cock out, stroking it slowly as he watches Dean finger himself. The bastard just unzipped his slacks and pulled his dick out while still in all his clothes. Benny’s cheeks and chest have a red blush across them, showing just how affected he is by Dean’s show. 

“Benny,” Dean whines, his fingers pumping faster. “Can I please use my new toy? Please tell me I can.”

“One more finger, Sweetheart. Get a third finger in your hole and then Cas’ll let you use your toy.”

Dean whimpers but obeys. He adds more lube to his fingers before pushing three into himself. It feels so good and Dean can’t wait to finally fuck himself with his new dildo, knowing it will fill him with such a perfect substitute. 

“Please,” Dean murmurs again, fucking himself relentlessly while he waits for Cas to give him the okay. His head is tilted back against the bed, not caring how he looks anymore because all that matters is getting his ass filled. 

“Okay, Dean,” Cas finally says. “Show us your new toy.”

Dean breathes a sigh of relief as he grabs his new dildo. “It’s called Pearce,” he tells them, bringing it in front of the camera for them to see. He holds it up to his face, licking a long strip up the side of it, feeling sexy while doing it. “I know you’ve been entertaining the idea, Benny. I thought I’d give it a try and tell you my thoughts.” 

“Dean,” Benny groans. The three of them have been talking about Benny getting a Prince Albert piercing for awhile now. Benny’s been leaning towards yes but he was nervous if it would actually feel as good for Dean and Cas as everyone implied it would. 

“Lube Pearce up,” Cas tells him with a smirk on his face. “But only push it in as far as the pink.”

The dildo Dean got is colored with pink at the tip, orange next, then yellow, then green. The base has blue and then purple. Dean has a feeling he’ll be teased beyond recognition before he’ll get that coveted green into his ass. 

Dean groans as he flips over, putting his feet on the floor and pushing his upper body against his bed. He adjusts until his cock lays down the side of the bed, pointing down towards his feet. To make sure he looks as good as he thinks he does, Dean picks up the small mirror by his head that he bought for this specific reason. He can see his laptop screen now and both of his boyfriends are staring at his ass and cock with their mouths open. He turns slightly so he can hold the mirror with his left hand by his right shoulder and use his right hand to hold the dildo. 

“Come on, Sweetheart. Wanna see you split open on that dildo while you think about what my cock is gonna feel like the next time you see me,” Benny says, his breathing coming out in pants now. 

Dean brings the lubed up dildo to his hole, watching himself on his screen to make sure he only goes up to the pink part. It stretches him just right as the head pops past his asshole. Dean can feel the piercing as it rubs against his inner walls and tugs on his rim everytime he pulls out and pushes it back in. 

“Please more,” he moans as he continues to tease his ass by just pushing the head of the dildo in and out of his hole. “Please.”

“Go ahead. Take it to the orange line,” Benny breaths. 

Dean watches as the dildo goes a little further, his thighs shaking with his restraint. He desperately wants to push the whole thing, watch his ass greedily take in every single inch of Pearce but he won’t. He wants to do as his boyfriends say. 

“So fucking beautiful, Cher.”

“Fuck, Dean. You have no idea what you’re doing to us right now. No idea how much we wish we were there with you.” Dean opens his eyes, not even realizing he had them closed to find them both jacking their cocks. Cas’ wet with how much precome he’s producing just watching Dean’s show. “Wanna see you bury that dildo in your ass, Dean. Fuck yourself, baby.”

Dean lets out a breathy, “thank you,” before slowly pushing the entire dildo into his ass, the balls at the bottom pressed against his cheeks. “Yes,” he cries as he begins to pump it in and out of his hole, loving the feeling of finally being full. “Fuck. I can feel the piercing. I can fucking feel it,” he whines as he angles the head to press against his prostate on every thrust. 

“Dean,” Benny groans, his gasps making Dean’s cock twitch where it lays against his comforter. When he looks at himself in the monitor of his laptop he can see precome dripping down between his legs and hitting the floor. Fuck. 

“I’m already so close,” Dean moans. “I want to come so badly but you both can’t come yet. Have one more surprise for you. Please let me come?”

Cas is the one who speaks, his voice so hoarse it’s almost like he’s so turned on he can barely get the words out. “Make yourself come, Dean.”

It only takes a few more precise thrusts against his prostate before Dean is coming, his warm cum dripping from the tip of his cock and sliding down the side of his bed down onto the floor. “Fuck!”

Dean lays his forehead against his bed, panting as his body goes limp. As gently as he can, Dean takes Pearce out of his well fucked ass and bringing it up towards his head. Without letting the boys see, he attaches the special tubbing to the base of his dildo. He grabs his large syringe filled with cum lube that he had warming in a bowl of steaming hot water. He pushes enough through that the tip of Pearce has a bead of cum showing before moving the dildo back to his ass. 

“Ready for your finale?” he asks, a cheeky smile on his face. 

“Yes,” Cas hisses through gritted teeth. “Show us, baby.”

Dean lazily fucks himself a few times before pushing the dildo about halfway in and pushing the syringe, feeling his ass fill with the warm cum lube. He moans, spreading his legs further so they’ll be able to see exactly what he’s just done. 

“Oh my god,” Benny moans as Dean slowly pulls the dildo from his hole. He tries to hold the cum in but it begins to slowly drip from his stretched hole. 

“Fuck, fuck, fuck,” Cas groans.

Dean gasps as he feels the warm liquid drip from his hole, passed his taint and down his balls. Then he pushes his muscles out, pushing the cum lube out forcibly and loving the noises that Benny begins to make. Both of his men have a kink for filling Dean up and either eating the cum out or watching it drip out. They love creampies and Dean is happy to deliver the fantasy. 

“Holy fucking shit,” Cas breathes, his head leaning against the back of his chair as his breathing returns to normal. 

Dean finally moves, sitting down on his bed and pulling his laptop back towards him. He smiles at the looks of absolute bliss on his boyfriends’ faces. “Good?”

“Fuck, Sugar. That was incredible. Money well spent,” Benny says with a chuckle. 

“Best placeholder I’ve ever had,” Dean agrees. 

“Oh fuck. Someone’s home,” Cas says grumpily. “I’ll talk to you both later. I love you.”

“Love you too, Cas,” Dean says. “Love you, Benny. Let me know when you schedule your piercing appointment.”

“Love you both too,” Benny says with a giant smile. “And I’m surprising you, Sweetheart. Bye.”

They log off and Dean sits back on his bed with a big, sated smile on his face. Only a few more months he reminds himself as he falls asleep.


End file.
